# US 12,225,812 B2 · Organic compound, light-emitting device, light-emitting apparatus, electronic device, and lighting device > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 12,225,812 B2 - Document ID: US12225812B2 - Status: Granted - Kind: B2 - Application number: 17/696,019 - Filed: 2022-03-16 - Published: 2022-10-13 - Granted: 2025-02-11 - Earliest claimed: 2021-03-31 - Assignees: Semiconductor Energy Laboratory Co., Ltd. - Applicants: Semiconductor Energy Laboratory Co., Ltd. - Inventors: Tomohiro Kubota; Takao Tosu; Takeyoshi Watabe; Airi Ueda; Yuta Kawano; Nobuharu Ohsawa; Satoshi Seo - Web page: https://patentgrep.com/patent/US12225812B2 ## CPC - C09K 11/06: containing organic luminescent materials - C07C 211/61: with at least one of the condensed ring systems formed by three or more rings - H10K 85/633: {comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom} - C07C 2603/18: Fluorenes; Hydrogenated fluorenes - C09K 2211/1007: Non-condensed systems - C09K 2211/1011: Condensed systems - C09K 2211/1014: bridged by heteroatoms, e.g. N, P, Si or B - H10K 50/15: Hole transporting layers - H10K 50/156: {comprising a multilayered structure} - H10K 85/342: {comprising iridium} - H10K 85/626: {containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene} - H10K 85/654: {comprising only nitrogen as heteroatom (H10K85/652 takes precedence)} - H10K 85/6572: {comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole} - H10K 85/6576: {comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene} - H10K 2101/30: Highest occupied molecular orbital [HOMO], lowest unoccupied molecular orbital [LUMO] or Fermi energy values - C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE - C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS - H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES ## Abstract An organic compound having a hole-transport property and a low refractive index is provided. An organic compound represented by General Formula (G1) shown below is provided. In General Formula (G1), Ar1 represents a substituted or unsubstituted arylene group having 6 to 13 carbon atoms in a ring, n represents an integer of 0 or 1, and Ar2 represents an aryl group having 6 to 10 carbon atoms in a ring and includes at least one branched-chain or cyclic alkyl group having 3 to 12 carbon atoms. The total number of carbon atoms of the branched-chain or cyclic alkyl group in Ar2 is more than or equal to 6. R1 to R4 each independently represent an alkyl group having 1 to 6 carbon atoms. R11 to R14 and R21 to R24 each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. Any one of R15 to R18 and any one of R25 to R28 each represent a bond directly bonded to a nitrogen atom, and the others each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. ## Claims ### Claim 1 An organic compound represented by General Formula (G1): wherein Ar1 represents a substituted or unsubstituted arylene group having 6 to 13 carbon atoms in a ring, wherein n represents 1, wherein Ar2 represents an aryl group having 6 to 10 carbon atoms in the ring and substituted with two or more substituents, each of the substituents comprising at least one branched-chain or cyclic alkyl group having 3 to 12 carbon atoms, wherein the total number of carbon atoms of the substituents in Ar2 is more than or equal to 6, wherein R1 to R4 each independently represent an alkyl group having 1 to 6 carbon atoms, wherein R11 to R14 each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, wherein any one of R15 to R18 represents a bond directly bonded to the nitrogen atom, and the others each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, wherein R21 to R24 each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and wherein any one of R25 to R28 represents a bond directly bonded to the nitrogen atom, and the others each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. ### Claim 2 An organic compound represented by General Formula (G2): wherein R1 to R4 each independently represent an alkyl group having 1 to 6 carbon atoms, wherein R11 to R14 each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, wherein any one of R15 to R18 represents a bond directly bonded to the nitrogen atom, and the others each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, wherein R21 to R24 each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, wherein any one of R25 to R28 represents a bond directly bonded to the nitrogen atom, and the others each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, wherein R31 to R35 each independently represent a hydrogen atom, a branched-chain alkyl group having 3 to 12 carbon atoms, or a cyclic alkyl group having 3 to 12 carbon atoms, and at least two of R31 to R35 each independently represent the branched-chain alkyl group having 3 to 12 carbon atoms or the cyclic alkyl group having 3 to 12 carbon atoms, wherein the total number of carbon atoms in R31 to R35 is more than or equal to 6, and wherein n represents an integer of 0 or 1. ### Claim 3 An organic compound represented by General Formula (G3): wherein R1 to R4 each independently represent an alkyl group having 1 to 6 carbon atoms, wherein R11 to R14 each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, wherein any one of R15 to R18 represents a bond directly bonded to the nitrogen atom, and the others each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, wherein R21 to R24 each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, wherein any one of R25 to R28 represents a bond directly bonded to the nitrogen atom, and the others each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, wherein R31, R32, R34, and R35 each represent a hydrogen atom, and wherein R33 represents a cyclic alkyl group having 3 to 12 carbon atoms and substituted with a branched-chain alkyl group having 3 to 12 carbon atoms. ### Claim 4 (depends on 1) The organic compound according to claim 1, wherein R11 to R14 and R21 to R24 each represent a hydrogen atom, wherein any one of R15 to R18 represents a bond directly bonded to the nitrogen atom, and the others each represent a hydrogen atom, and wherein any one of R25 to R28 represents a bond directly bonded to the nitrogen atom, and the others each represent a hydrogen atom. ### Claim 5 (depends on 2) The organic compound according to claim 2, wherein R11 to R14 and R21 to R24 each represent a hydrogen atom, wherein any one of R15 to R18 represents a bond directly bonded to the nitrogen atom, and the others each represent a hydrogen atom, and wherein any one of R25 to R28 represents a bond directly bonded to the nitrogen atom, and the others each represent a hydrogen atom. ### Claim 6 (depends on 2) The organic compound according to claim 2, wherein the General Formula (G2) is represented by General Formula (G4): ### Claim 7 (depends on 2) The organic compound according to claim 2, wherein at least two of R31 to R35 each represent a tert-butyl group or a cyclohexyl group. ### Claim 8 (depends on 2) The organic compound according to claim 2, wherein R31, R33, and R35 each represent a hydrogen atom, and wherein R32 and R34 each represent a tert-butyl group or a cyclohexyl group. ### Claim 9 (depends on 2) The organic compound according to claim 2, wherein the General Formula (G2) is represented by Structural Formula (100) or (101): ### Claim 10 (depends on 1) A light-emitting device comprising the organic compound according to claim 1. ### Claim 11 (depends on 10) An electronic device comprising: the light-emitting device according to claim 10; and at least one of a sensor unit, an input unit, and a communication unit. ### Claim 12 (depends on 10) A light-emitting apparatus comprising: the light-emitting device according to claim 10; and at least one of a transistor and a substrate. ### Claim 13 (depends on 10) A lighting device comprising: the light-emitting device according to claim 10; and a housing. ### Claim 14 (depends on 3) The organic compound according to claim 3, wherein R11 to R14 and R21 to R24 each represent a hydrogen atom, wherein any one of R15 to R18 represents a bond directly bonded to the nitrogen atom, and the others each represent a hydrogen atom, and wherein any one of R25 to R28 represents a bond directly bonded to the nitrogen atom, and the others each represent a hydrogen atom. ### Claim 15 (depends on 3) The organic compound according to claim 3, wherein the General Formula (G3) is represented by General Formula (G4): ### Claim 16 (depends on 2) A light-emitting device comprising the organic compound according to claim 2. ### Claim 17 (depends on 3) A light-emitting device comprising the organic compound according to claim 3.